Ethyl Acetate → (R)-1-[2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide

HRID 400075Notes

Reaction equation

HRID 400075 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH2:28][CH2:29]CS([O-])(=O)=O)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([C:43]([NH2:45])=[O:44])[CH2:39][CH2:38]1.[C:46]1([C:52]2([C:58]([OH:60])=[O:59])[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(OCC)(=O)C>CO.ClCCl>[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([C:43]([NH2:45])=[O:44])[CH2:39][CH2:38]1.[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH2:28][CH2:29][N:55]3[CH2:54][CH2:53][C:52]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)([C:58]([OH:60])=[O:59])[CH2:57][CH2:56]3)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 675621544-Phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide hydrochlorideHCID 86753250(S)-2-[1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate

Product 1

HCID 131720899(R)-1-[2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent3×

Procedure

Prepare by the method of Example 88.6 using (S)-2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate and 4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide hydrochloride to give, after chromatography on silica gel eluting sequentially with ethyl acetate, 3% methanol/dichloromethane, 6% methanol/dichloromethane, and then 10% methanol/dichloromethane, the title compound: Rf =0.41 (silica gel, 6% methanol/dichloromethane).

Workup

  1. customto give

Sources & evidence

ORD record
ord-194f7e422b8f446f925867dc784867c5
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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